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Royal Society of Chemistry, Organic and Biomolecular Chemistry, 27(12), p. 4816-4819, 2014

DOI: 10.1039/c4ob00741g

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Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates

Journal article published in 2014 by S. Mandal, U. J. Nilsson ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

Tri-isopropylsilyl thio-glycosides (TIPS S-glycosides) were synthesized through base promoted SN2 substitution of glycosyl halides with TIPS-SH or by Lewis acid promoted glycosylation of TIPS-SH with glycosyl acetates or p-methoxyphenyl glycosides. Various thioglycoside derivatives were obtained in high yields by one-pot fluoride-mediated de-silylation and thiol alkylation with alkyl halides or Michael acceptors of one common TIPS S-glycoside.